Part of my coaching service includes advising clients on what to book when, so that after our week of working together, they have a plan to create their trip. Usually they contact me ready to go: let’s plan, let’s book! they say. The enthusiasm is wonderful, but trying to book everything at the same time is not the best use of your time. Instead, I recommend the approach below, which I use when I create gold and platinum Italy itineraries.

Book accommodations at least 4 months in advance, unless you’re going in August or renting a villa.

When I worked in Milan as an expat, the January espresso machine chat centered almost completely around August vacation planning. Italians book their August vacations in January, and so should you. Villa rental also needs to be done early — it really depends on the villa (and I can always find something) but for the best selection and the best experience, book 9 months+ in advance. But for hotels, farmhouses, B&Bs, apartments, castles, and other accommodation, aim to book 4-6 months in advance for a good selection (or, if you’re not ready to commit, find your top three, book all three, noting the cancellation window, and then cancel later).

Book classes and short tours about 3 months in advance, unless it’s a rock star teacher.

Often, if you try to book classes or day tours more than 3 months in advance, you’ll be told to call back later. Either the schedule isn’t set, or they just aren’t taking bookings, and it goes in to your must-follow-up-on list. I’m not saying that you won’t be able to book earlier than that, but you’ll have plenty of options 3 months ahead of time and you won’t be told to call back.

Book car rentals about 2 months in advance.

Car rental prices change according to some algorithm I don’t understand, but what I do know is that if you book really early, the price is higher compared to about 8 weeks pre-departure (for an automatic transmission). If you can drive a stick shift, you can book 6 or even 5 weeks before departure. At about 4 weeks out, prices start to creep up. I start watching rates starting about 6 months pre-departure and most of the time I confirm the car rental about 8 weeks pre-departure.

Book tickets about 6 weeks in advance.

For small festivals (even ones that happen yearly) or anything that requires a schedule of performances, it’s completely normal for the schedule to be released about 6 weeks beforehand, or less. Major venues like Milan’s La Scala Opera house or comparable venues are released and have tickets available for booking months in advance, but the smaller and more local the festival, the later the schedule will be published. Even if you don’t need tickets, and are just interested in a local food festival, expect the schedule to be published (most likely only in Italian) 4-ish weeks ahead of time.

Book restaurants about a week in advance, unless they have Michelin stars.

For the hard-to-get reservation, how far in advance you need to book varies wildly, but in general, Michelin-starred restaurants can be booked a month or two in advance. For everything else, there’s no point booking more than about a week to ten days before you plan to dine. In Rome, Florence, and Venice, restaurants are accustomed to taking reservations from tourists weeks ahead of time, but when I’ve tried to call restaurants in smaller or more remote places that early, they always ask me to please just call back.

There are, of course, exceptions to every rule, but for the vast majority of trips, following this advice will allow you to make a decision, confirm it once, and check it off your list. And if you don’t want to do it? Contact me at italybto@gmail.com — I’d love to do it for you.